Evidence for ketene intermediates in the reactions of 2-oxobutanedioic acid diesters with alcohols and water

…, RL Titus, RM Gonzalez

Index: Emerson, David W.; Titus, Richard L.; Gonzalez, Rowena M. Journal of Organic Chemistry, 1990 , vol. 55, # 11 p. 3572 - 3576

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Citation Number: 7

Abstract

The reactions of the diethyl ester (la) and dimethyl ester (lb) of 3-methyl-2-oxobutanedioic acid with excess ethanol, methanol, or water in a sealed tube at approximately 125" C were studied. With methanol, la yielded mainly 3-methyl-2-oxobutanedioic acid 1-ethyl 4-methyl diester, 2a; with ethanol, lb yielded mainly the 4-ethyl 1-methyl diester, 2b, while reaction of la with water yielded carbon dioxide, 2-oxobutanoic acid ethyl ester, 6, and 2-methyl-3- ...